Mac only: iPods are great, but if you want to sync your music with another device—like a Sansa Clip or an Android phone—iTunes doesn't exactly have your back. Middleman is a free service for iTunes that syncs a playlist of your choice with any USB mass storage device.

Android now have apps like previously mentioned iSyncr to sync their devices with iTunes, but those of us using plain ol' USB drives or other USB-based MP3 players are still left out in the cold. We just want something simple and free to copy our music. Middleman hopes to fill this void. It isn't the prettiest or the most feature-filled, but it'll sync your music to nearly any device with little hassle.

What it does: Lets you select any playlist from iTunes and sync the tracks contained within to any desired folder on your USB mass-storage device.

Installation: Middleman is a Service that can be launched straight from iTunes. To install it, just mount the DMG, drag the Middleman_temp file to the Library folder in "Macintosh HD", and double-click on the "Sync selected playlist" file.

As always, we recommend you make sure all your data is backed up before using a new program that moves your files around. We've tested this pretty thoroughly, but you never know what could go wrong.

Usage: Middleman requires a bit of initial setup. Due to the nature of iTunes and Middleman, you can only sync one playlist to your device. If you try to sync a second playlist, it'll delete tracks from the first playlist. So, if you aren't syncing your entire library, create one master "Sync" playlist with all the tracks you want on your device. My preferred way of creating the master playlist is to create a smart playlist that includes all the playlists I want to sync, but you can do this any way you want.

To sync, mount your device and select your master playlist in iTunes (or, if you're syncing your whole library, just select "Music"). In the menu bar, go to iTunes -> Services -> Sync Selected Playlist with Middleman. Middleman will prompt you for the folder on your device in which you want to sync your music. You can select any folder you want, including the root folder of your device—it will not delete the contents of the folder you choose; it will put the music in another folder named "Middleman" inside of it. It will use your existing directory structure for artists and albums, so I highly recommend you have the "Keep iTunes Media Folder Organized" box checked under Preferences > Advanced in iTunes.

Middleman will show a dialog that says it is gathering information, which may take a few minutes depending on the size of the playlist you're syncing (the spinning gear in the menu bar shows that it's working). When it's done, your device will begin syncing (you'll see it all happening in a Terminal window), showing you the progress track-by-track. As always, the first sync takes a while, but subsequent syncs will only transfer new or changed songs (and will remove from the device songs no longer on the master playlist). When it finishes syncing, you may close or quit Terminal and unmount your device.

Note that Middleman doesn't sync any playlists, just the tracks listed on the playlist you sync. I couldn't find an easy way, with my knowledge and skill set, to sync the playlists themselves too. For now, you're best off using something like iTunes Export, which will convert any number of playlists from iTunes to .M3U format and put them on your device if you so choose. Keep in mind you'll need the tracks on those playlists synced to your device for them to work.

Middleman is a free download for Mac OS 10.6 Snow Leopard and 10.7 Lion only. Middleman was made in Automator, using a number of Applescripts, and relies heavily on rsync, which is built into OS X. If you would like to view or edit the workflow in Automator, just navigate to ~/Library/Services and double click on the Sync Selected Playlist with Middleman workflow.

Bug reports and feature requests: I've thoroughly tested Middleman on my machine and a few others, but it's had little exercise outside of that. If you find a bug, have a good idea for a new feature, or know a little about Applescript and Automator and have a suggestion/improvement to offer, leave a comment below.